WO2004106275A2 - Compounds useful in the therapy of alzheimer’s disease and formulations containing them - Google Patents
Compounds useful in the therapy of alzheimer’s disease and formulations containing them Download PDFInfo
- Publication number
- WO2004106275A2 WO2004106275A2 PCT/EP2004/005644 EP2004005644W WO2004106275A2 WO 2004106275 A2 WO2004106275 A2 WO 2004106275A2 EP 2004005644 W EP2004005644 W EP 2004005644W WO 2004106275 A2 WO2004106275 A2 WO 2004106275A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- salt
- octahydrohyperforin
- salts
- galantamine
- alzheimer
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/743—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups having unsaturation outside the rings, e.g. humulones, lupulones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/723—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic
- C07C49/727—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system
- C07C49/733—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups polycyclic a keto group being part of a condensed ring system having two rings
Definitions
- the present invention concerns floroglucinol salts with acetylcholinesterase-inhibiting alkaloids and methods for the preparation thereof.
- Amyloid peptide A ⁇ l-42 a product of transformation of Alzheimer Precursor Protein (APP), plays as key role in the appearance of Alzheimer's disease ⁇ Nature Medicine, 3, 28-29, 1997; Science, 275, 630-1, 1997).
- NMDA antagonistic alkaloids e.g. memantine
- nootropics cholinergics
- glutamine antagonists e.g. glutamine antagonists
- serotoninergics e.g. glutamine antagonists
- MAO inhibitors e.g. glutamine antagonists
- PKC activators e.g. PKC activators
- muscarinic agonists may also be conveniently used to this purpose.
- Hyperforin salts with anticholinesterase alkaloids were recently disclosed in WO/99/41220 as particularly interesting for the treatment of Alzheimer's disease. It has however been subsequently observed that the pharmacological activity of said salts decreases in vivo due to metabolic reactions.
- floroglucinol salts in particular salts of tetrahydro- and octahydro-hyperforin or adhyperforin derivatives and of colupolon with alkaloids, are metabolically stable and induce higher ⁇ -secretase activity compared to the single compounds and the salts described in WO/99/41220.
- - n is 0 or 1 ;
- formulae (II) and (III) also including the corresponding tautomeric forms; and [B] is the cation of an alkaloid selected from: anticholinesterase agents, NMDA-antagonists, nootropics, cholinergics, glutamine antagonists, serotoninergics, MAO inhibitors, PKC activators, muscarinic agonists, vincamine, apovincamine, chinidine and eseroline.
- an alkaloid selected from: anticholinesterase agents, NMDA-antagonists, nootropics, cholinergics, glutamine antagonists, serotoninergics, MAO inhibitors, PKC activators, muscarinic agonists, vincamine, apovincamine, chinidine and eseroline.
- Preferred anticholinesterase agents are galantamine, physostigmine, huperzine and tacrine; a preferred NMDA-antagonist is memantine.
- octahydrohyperforin salt with galantamine octahydrohyperforin salt with physostigmine; octahydrohyperforin salt with memantine; octahydrohyperforin salt with vincamine; octahydrohyperforin salt with apovincamine; octahydrohyperforin salt with chinidine; octahydrohyperforin salt with eseroline; octahydrohyperforin salt with tacrine; galantamine salt with colupolon.
- Hyperforin and adhyperforin saturated derivatives can be obtained by direct reduction of hexane or ether extracts enriched in the Hypericum perforatum flowering tops.
- the tetrahydro-derivatives can be obtained by reduction with hydrides, whereas the octahydro-derivatives can be obtained by chemoselective reduction of the isoprene chains by catalytic hydrogenation, as described WO 03/091 14.
- Hyperforin derivatives and colupolon are salified with the above mentioned alkaloids according to conventional methods, well known to those skilled in the art.
- the salts according to the present invention are stable crystalline products having strong antidepressive and anti- Alzheimer actions.
- the effect of the compounds of the invention on ⁇ -secretase-induced APPs release was determined in the culture medium of a neuroblastoma cell line (SH-SY5Y) according to what reported by Galbete J.L. et al. in Biochem. 348,307-313, 2000.
- the results reported in the following Table show that the tested compounds activate ⁇ -secretase-mediated APP metabolism inducing an increase in APPs secreted in the culture medium.
- the compounds of the invention are active both as acetylcholinesterase inhibitors and protein kinase C activators.
- Example II Octahydrohyperforin salt with physostigmine Following the procedure described in Example I, physostigmine base is salified with an octahydrohyperforin equivalent. Physostigmine octahydrohyperforinate is obtained, having the following physico-chemical and spectroscopic characteristics:
- Example XI Transdermal plaster containing galantamine octahydrohyperforinate
- Example XII Transdermal plaster containing mentamine octahydrohyperforinate
- 0.050 g of mentamine octahydrohyperforinate were suspended in 10 g of a medical silicone adhesive (Dow Corning MD7-4502) to give a gel of the medicament.
- the gel was deposited with solvent onto a polyester film (S2016) by means of a coating apparatus. After drying at 80°C for 10 minutes, a polyester film (Scotchpack 1 109) was laminated onto the gel of dried medicament and the resulting sheet was cut into plasters of the desired size.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04739354A EP1638914A2 (de) | 2003-05-30 | 2004-05-26 | Verbindungen zur behandlung der alzheimerschen krankheit und diese verbindungen enthaltende formulierungen |
CA002527354A CA2527354A1 (en) | 2003-05-30 | 2004-05-26 | Compounds useful in the therapy of alzheimer`s disease and formulations containing them |
BRPI0410703-9A BRPI0410703A (pt) | 2003-05-30 | 2004-05-26 | compostos úteis na terapia da doença de alzheimer e formulações contendo os mesmos |
MXPA05012826A MXPA05012826A (es) | 2003-05-30 | 2004-05-26 | Compuestos utiles en la terapia de la enfermedad de alzheimer y formulaciones que los contienen. |
JP2006529917A JP2007505152A (ja) | 2003-05-30 | 2004-05-26 | アルツハイマー病の治療に有効な化合物およびそれら化合物を含む製剤 |
AU2004242838A AU2004242838A1 (en) | 2003-05-30 | 2004-05-26 | Compounds useful in the therapy of Alzheimer's disease and formulations containing them |
US10/558,403 US20070010507A1 (en) | 2003-05-30 | 2005-05-26 | Compounds useful in the therapy of alzheimer's disease and formulations containing them |
EC2005006190A ECSP056190A (es) | 2003-05-30 | 2005-11-28 | Compuestos utiles en la terapia de la enfermedad de alzheimer y formulaciones que los contienen |
IL172213A IL172213A0 (en) | 2003-05-30 | 2005-11-28 | Compounds useful in the therapy of alzheimer's disease and formulations containing them |
NO20056042A NO20056042L (no) | 2003-05-30 | 2005-12-19 | Forbindelser som er anvendelige til behandling av Alzheimers sykdom samt formuleringer inneholdende disse |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT001098A ITMI20031098A1 (it) | 2003-05-30 | 2003-05-30 | Composti utili nella terapia del morbo di alzheimer e formulazioni che li contengono |
ITMI2003A001098 | 2003-05-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2004106275A2 true WO2004106275A2 (en) | 2004-12-09 |
WO2004106275A3 WO2004106275A3 (en) | 2005-03-17 |
Family
ID=30131121
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/005644 WO2004106275A2 (en) | 2003-05-30 | 2004-05-26 | Compounds useful in the therapy of alzheimer’s disease and formulations containing them |
Country Status (16)
Country | Link |
---|---|
US (1) | US20070010507A1 (de) |
EP (1) | EP1638914A2 (de) |
JP (1) | JP2007505152A (de) |
KR (1) | KR20060012316A (de) |
CN (1) | CN1795158A (de) |
AU (1) | AU2004242838A1 (de) |
BR (1) | BRPI0410703A (de) |
CA (1) | CA2527354A1 (de) |
DE (1) | DE602004010100T2 (de) |
EC (1) | ECSP056190A (de) |
IL (1) | IL172213A0 (de) |
IT (1) | ITMI20031098A1 (de) |
MX (1) | MXPA05012826A (de) |
NO (1) | NO20056042L (de) |
RU (1) | RU2005136984A (de) |
WO (1) | WO2004106275A2 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007035941A2 (en) * | 2005-09-23 | 2007-03-29 | Alza Corporation | Transdermal galantamine delivery system |
EP1898729A2 (de) * | 2005-06-21 | 2008-03-19 | John I. Haas, Inc. | Zusammensetzungen, die anorganische salze von hopfensäuren enthalten, sowie verfahren zu ihrer herstellung |
EP2236160A3 (de) * | 2009-03-31 | 2011-12-14 | Sanovel Ilac Sanayi ve Ticaret A.S. | Dimebolin enthaltende Zusammensetzungen mit modifizierter Freisetzung |
WO2011157416A2 (de) | 2010-06-17 | 2011-12-22 | Lts Lohmann Therapie-Systeme Ag | Transdermale verabreichung von memantin |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2776498A1 (en) * | 2009-10-02 | 2011-04-07 | Blanchette Rockefeller Neurosciences Institute | Abnormal alterations of pkc isozymes processing in alzheimer's disease peripheral cells |
EP3328374A4 (de) * | 2015-07-31 | 2019-03-13 | The Johns Hopkins University | Glutaminantagonisten zur behandlung von kognitiven defiziten |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999041220A1 (de) * | 1998-02-13 | 1999-08-19 | Dr. Willmar Schwabe Gmbh & Co. | Stabile hyperforin-salze, verfahren zu ihrer herstellung und verwendung zur therapie der alzheimerschen krankheit |
WO2000054785A2 (en) * | 1999-03-15 | 2000-09-21 | Shaman Pharmaceuticals, Inc. | Stabilized bicyclo[3.3.1]nonenes and methods of use |
WO2003035007A2 (en) * | 2001-10-26 | 2003-05-01 | Metaproteomics, Llc | Curcuminoid compositions exhibiting synergistic inhibition of the expression and/or activity of cyclooxygenase-2 |
-
2003
- 2003-05-30 IT IT001098A patent/ITMI20031098A1/it unknown
-
2004
- 2004-05-26 AU AU2004242838A patent/AU2004242838A1/en not_active Abandoned
- 2004-05-26 MX MXPA05012826A patent/MXPA05012826A/es not_active Application Discontinuation
- 2004-05-26 RU RU2005136984/04A patent/RU2005136984A/ru not_active Application Discontinuation
- 2004-05-26 EP EP04739354A patent/EP1638914A2/de not_active Withdrawn
- 2004-05-26 KR KR1020057022409A patent/KR20060012316A/ko not_active IP Right Cessation
- 2004-05-26 CA CA002527354A patent/CA2527354A1/en not_active Abandoned
- 2004-05-26 BR BRPI0410703-9A patent/BRPI0410703A/pt not_active IP Right Cessation
- 2004-05-26 JP JP2006529917A patent/JP2007505152A/ja active Pending
- 2004-05-26 WO PCT/EP2004/005644 patent/WO2004106275A2/en active Application Filing
- 2004-05-26 CN CNA2004800146347A patent/CN1795158A/zh active Pending
- 2004-05-28 DE DE602004010100T patent/DE602004010100T2/de not_active Expired - Lifetime
-
2005
- 2005-05-26 US US10/558,403 patent/US20070010507A1/en not_active Abandoned
- 2005-11-28 EC EC2005006190A patent/ECSP056190A/es unknown
- 2005-11-28 IL IL172213A patent/IL172213A0/en unknown
- 2005-12-19 NO NO20056042A patent/NO20056042L/no unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999041220A1 (de) * | 1998-02-13 | 1999-08-19 | Dr. Willmar Schwabe Gmbh & Co. | Stabile hyperforin-salze, verfahren zu ihrer herstellung und verwendung zur therapie der alzheimerschen krankheit |
WO2000054785A2 (en) * | 1999-03-15 | 2000-09-21 | Shaman Pharmaceuticals, Inc. | Stabilized bicyclo[3.3.1]nonenes and methods of use |
WO2003035007A2 (en) * | 2001-10-26 | 2003-05-01 | Metaproteomics, Llc | Curcuminoid compositions exhibiting synergistic inhibition of the expression and/or activity of cyclooxygenase-2 |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1898729A2 (de) * | 2005-06-21 | 2008-03-19 | John I. Haas, Inc. | Zusammensetzungen, die anorganische salze von hopfensäuren enthalten, sowie verfahren zu ihrer herstellung |
EP1898729A4 (de) * | 2005-06-21 | 2009-05-06 | Haas Inc John I | Zusammensetzungen, die anorganische salze von hopfensäuren enthalten, sowie verfahren zu ihrer herstellung |
WO2007035941A2 (en) * | 2005-09-23 | 2007-03-29 | Alza Corporation | Transdermal galantamine delivery system |
WO2007035941A3 (en) * | 2005-09-23 | 2007-05-18 | Alza Corp | Transdermal galantamine delivery system |
EP2236160A3 (de) * | 2009-03-31 | 2011-12-14 | Sanovel Ilac Sanayi ve Ticaret A.S. | Dimebolin enthaltende Zusammensetzungen mit modifizierter Freisetzung |
WO2011157416A2 (de) | 2010-06-17 | 2011-12-22 | Lts Lohmann Therapie-Systeme Ag | Transdermale verabreichung von memantin |
DE102010024105A1 (de) | 2010-06-17 | 2011-12-22 | Grünenthal GmbH | Transdermale Verabreichung von Memantin |
US10363228B2 (en) | 2010-06-17 | 2019-07-30 | Lts Lohmann Therapie-Systeme Ag | Transdermal administration of memantine |
Also Published As
Publication number | Publication date |
---|---|
CN1795158A (zh) | 2006-06-28 |
ECSP056190A (es) | 2006-08-30 |
MXPA05012826A (es) | 2006-02-13 |
AU2004242838A1 (en) | 2004-12-09 |
DE602004010100T2 (de) | 2008-09-18 |
WO2004106275A3 (en) | 2005-03-17 |
DE602004010100D1 (de) | 2007-12-27 |
RU2005136984A (ru) | 2006-03-27 |
US20070010507A1 (en) | 2007-01-11 |
ITMI20031098A0 (it) | 2003-05-30 |
IL172213A0 (en) | 2009-02-11 |
KR20060012316A (ko) | 2006-02-07 |
ITMI20031098A1 (it) | 2004-11-30 |
JP2007505152A (ja) | 2007-03-08 |
NO20056042L (no) | 2005-12-19 |
BRPI0410703A (pt) | 2006-06-13 |
CA2527354A1 (en) | 2004-12-09 |
EP1638914A2 (de) | 2006-03-29 |
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